Boron-nitrogen-containing organic compounds, and uses thereof in organic electronic devices

Abstract

A boron-nitrogen-containing organic compound includes a structure of one of formula (I)-formula (IV). A formulation contains at least one organic solvent, and at least one boron-nitrogen-containing organic compound. An organic electronic device contains at least one boron-nitrogen-containing organic compound. The boron-nitrogen-containing organic compound is applied to the organic device. The device utilizing the boron-nitrogen-containing organic compound exhibits high luminescence efficiency, narrow emission spectrum FWHM, long operation lifetime, etc.

What is claimed is: 
     
         1 . A boron-nitrogen-containing organic compound, comprising a structure of one of formula (I)-formula (IV): 
       
         
           
           
               
               
           
         
         wherein: 
         each of Q 1  ring and Q 2  ring at each occurrence is independently selected from a substituted/unsubstituted aryl group, a substituted/unsubstituted heteroaryl group, or a substituted/unsubstituted fused-ring structure; 
         each X is independently selected from B, N, P, P═O, or Al; 
         each of Y 1  and Y 2  at each occurrence is independently selected from C═O, N—R 1 , O, S, Se, P, P═O, or P═S; 
         each V 0  at each occurrence is independently C—R 2  or N; 
         each of V 1  to V 3  at each occurrence is independently C—R 3  or N; 
         each of R and R 1 -R 3  at each occurrence is independently selected from —H, -D, a C 1 -C 20  linear alkyl group, a C 1 -C 20  linear alkoxy group, a C 1 -C 20  linear thioalkoxy group, a C 3 -C 20  branched/cyclic alkyl group, a C 3 -C 20  branched/cyclic alkoxy group, a C 3 -C 20  branched/cyclic thioalkoxy group, a C 3 -C 20  branched/cyclic silyl group, a C 1 -C 20  ketone group, a C 2 -C 20  alkoxycarbonyl group, a C 7 -C 20  aryloxycarbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, —CF 3 , —Cl, —Br, —F, a cross-linkable group, a substituted/unsubstituted aromatic or heteroaromatic group containing 5 to 60 ring atoms, an aryloxy or heteroaryloxy group containing 5 to 60 ring atoms, or any combination thereof, and one or more R 3 s form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and/or with the rings bonded thereto. 
       
     
     
         2 . The boron-nitrogen-containing organic compound according to  claim 1 , wherein the boron-nitrogen-containing organic compound comprises a structure of one of formulas (I-1)-(IV-1): 
       
         
           
           
               
               
           
         
       
     
     
         3 . The boron-nitrogen-containing organic compound according to  claim 1 , wherein the boron-nitrogen-containing organic compound comprises a structure of one of formulas (I-2)-(IV-2): 
       
         
           
           
               
               
           
         
         wherein, each V 4  at each occurrence is independently C—R 3  or N. 
       
     
     
         4 . The boron-nitrogen-containing organic compound according to  claim 2 , wherein the boron-nitrogen-containing organic compound comprises a structure of one of formulas (I-2)-(IV-2): 
       
         
           
           
               
               
           
         
         wherein, each V 4  at each occurrence is independently C—R 3  or N. 
       
     
     
         5 . The boron-nitrogen-containing organic compound according to  claim 1 , wherein Q 1  ring at each occurrence is independently selected from one or combinations of more than one of the following structures: 
       
         
           
           
               
               
           
         
         wherein, each V at each occurrence is independently C—R 4  or N; 
         each W at each occurrence is independently selected from B—R 5 , C(═O), N—R 6 , O, S, P, P═O, or P═S; 
         each of R 4  to R 6  at each occurrence is independently selected from —H, -D, a C 1 -C 20  linear alkyl group, a C 1 -C 20  linear alkoxy group, a C 1 -C 20  linear thioalkoxy group, a C 3 -C 20  branched/cyclic alkyl group, a C 3 -C 20  branched/cyclic alkoxy group, a C 3 -C 20  branched/cyclic thioalkoxy group, a C 3 -C 20  branched/cyclic silyl group, a C 1 -C 20  ketone group, a C 2 -C 20  alkoxycarbonyl group, a C 7 -C 20  aryloxycarbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, —CF 3 , —Cl, —Br, —F, a cross-linkable group, a substituted/unsubstituted aromatic or heteroaromatic group containing 5 to 40 ring atoms, an aryloxy or heteroaryloxy group containing 5 to 40 ring atoms, or any combination thereof, wherein one or more R 4 -R 6  form a ring system with each other and/or with the groups bonded thereto. 
       
     
     
         6 . The boron-nitrogen-containing organic compound according to  claim 2 , wherein Q 1  ring at each occurrence is independently selected from one or combinations of more than one of the following structures: 
       
         
           
           
               
               
           
         
         wherein, each V at each occurrence is independently C—R 4  or N; 
         each W at each occurrence is independently selected from B—R 5 , C(═O), N—R 6 , O, S, P, P═O, or P═S; 
         each of R 4  to R 6  at each occurrence is independently selected from —H, -D, a C 1 -C 20  linear alkyl group, a C 1 -C 20  linear alkoxy group, a C 1 -C 20  linear thioalkoxy group, a C 3 -C 20  branched/cyclic alkyl group, a C 3 -C 20  branched/cyclic alkoxy group, a C 3 -C 20  branched/cyclic thioalkoxy group, a C 3 -C 20  branched/cyclic silyl group, a C 1 -C 20  ketone group, a C 2 -C 20  alkoxycarbonyl group, a C 7 -C 20  aryloxycarbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, —CF 3 , —Cl, —Br, —F, a cross-linkable group, a substituted/unsubstituted aromatic or heteroaromatic group containing 5 to 40 ring atoms, an aryloxy or heteroaryloxy group containing 5 to 40 ring atoms, or any combination thereof, wherein one or more R 4 -R 6  form a ring system with each other and/or with the groups bonded thereto. 
       
     
     
         7 . The boron-nitrogen-containing organic compound according to  claim 3 , wherein Q 1  ring at each occurrence is independently selected from one or combinations of more than one of the following structures: 
       
         
           
           
               
               
           
         
         wherein, each V at each occurrence is independently C—R 4  or N; 
         each W at each occurrence is independently selected from B—R 5 , C(═O), N—R 6 , 0, S, P, P═O, or P═S; 
         each of R 4  to R 6  at each occurrence is independently selected from —H, -D, a C 1 -C 20  linear alkyl group, a C 1 -C 20  linear alkoxy group, a C 1 -C 20  linear thioalkoxy group, a C-2 branched/cyclic alkyl group, a C 3 -C 20  branched/cyclic alkoxy group, a C 3 -C 20  branched/cyclic thioalkoxy group, a C 3 -C 20  branched/cyclic silyl group, a C 1 -C 20  ketone group, a alkoxycarbonyl group, a C 7 -C 20  aryloxycarbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, —CF 3 , —Cl, —Br, —F, a cross-linkable group, a substituted/unsubstituted aromatic or heteroaromatic group containing 5 to 40 ring atoms, an aryloxy or heteroaryloxy group containing 5 to 40 ring atoms, or any combination thereof, wherein one or more R 4 -R 6  form a ring system with each other and/or with the groups bonded thereto. 
       
     
     
         8 . The boron-nitrogen-containing organic compound according to  claim 4 , wherein Q 1  ring at each occurrence is independently selected from one or combinations of more than one of the following structures: 
       
         
           
           
               
               
           
         
         wherein, each V at each occurrence is independently C—R 4  or N; 
         each W at each occurrence is independently selected from B—R 5 , C(═O), N—R 6 , O, S, P, P═O, or P═S; 
         each of R 4  to R 6  at each occurrence is independently selected from —H, -D, a C 1 -C 20  linear alkyl group, a C 1 -C 20  linear alkoxy group, a C 1 -C 20  linear thioalkoxy group, a C 3 -C 20  branched/cyclic alkyl group, a C 3 -C 20  branched/cyclic alkoxy group, a C 3 -C 20  branched/cyclic thioalkoxy group, a C 3 -C 20  branched/cyclic silyl group, a C 1 -C 20  ketone group, a C 2 -C 20  alkoxycarbonyl group, a C 7 -C 20  aryloxycarbonyl group, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, —CF 3 , —Cl, —Br, —F, a cross-linkable group, a substituted/unsubstituted aromatic or heteroaromatic group containing 5 to 40 ring atoms, an aryloxy or heteroaryloxy group containing 5 to 40 ring atoms, or any combination thereof, wherein one or more R 4 -R 6  form a ring system with each other and/or with the groups bonded thereto. 
       
     
     
         9 . A formulation, comprising at least one organic solvent, and at least one of the boron-nitrogen-containing organic compound according to  claim 1 . 
     
     
         10 . An organic electronic device, comprising at least one of the boron-nitrogen-containing organic compound according to  claim 1 . 
     
     
         11 . The organic electronic device according to  claim 10 , wherein the organic electronic device is selected from a color converter, an organic light-emitting diode, an organic photovoltaic cell, an organic light emitting electrochemical cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic electronic device, an organic sensor, or an organic plasmon emitting diode. 
     
     
         12 . The organic electronic device according to  claim 10 , wherein the organic electronic device is an organic light-emitting device, the organic light-emitting device comprises a light-emitting layer, a dopant material of the light-emitting layer comprises at least one of the boron-nitrogen-containing organic compound.